RU2249461C2 - Включающие циклоспорин композиции, практически не содержащие масла - Google Patents

Включающие циклоспорин композиции, практически не содержащие масла Download PDF

Info

Publication number: RU2249461C2
Authority: RU; Russia
Prior art keywords: composition; cyclosporin; capsule; lipophilic; fatty acid
Prior art date: 1999-05-28

Application number

RU2001133455/15A

Other languages

English (en)

Russian (ru)

Other versions

RU2001133455A (ru

Inventor

Михаэль АМБЮЛЬ (CH)

Михаэль АМБЮЛЬ

Барбара ЛЮККЕЛЬ (DE)

Барбара ЛЮККЕЛЬ

Барбара ХЭБЕРЛИН (CH)

Барбара ХЭБЕРЛИН

Армин МАЙНЦЕР (DE)

Армин МАЙНЦЕР

Original Assignee

Новартис Аг

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1999-05-28

Filing date

2000-05-26

Publication date

2005-04-10

2000-05-26 Application filed by Новартис Аг filed Critical Новартис Аг

2003-08-20 Publication of RU2001133455A publication Critical patent/RU2001133455A/ru

2005-04-10 Application granted granted Critical

2005-04-10 Publication of RU2249461C2 publication Critical patent/RU2249461C2/ru

Links

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Classifications

- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4858—Organic compounds
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/12—Cyclic peptides, e.g. bacitracins; Polymyxins; Gramicidins S, C; Tyrocidins A, B or C
- A61K38/13—Cyclosporins
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
- A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P41/00—Drugs used in surgical methods, e.g. surgery adjuvants for preventing adhesion or for vitreum substitution
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

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Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
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Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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Gastroenterology & Hepatology (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Transplantation (AREA)
Orthopedic Medicine & Surgery (AREA)
Physical Education & Sports Medicine (AREA)
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Toxicology (AREA)
Pain & Pain Management (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Medicinal Preparation (AREA)
Peptides Or Proteins (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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RU2001133455/15A 1999-05-28 2000-05-26 Включающие циклоспорин композиции, практически не содержащие масла RU2249461C2 (ru)

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GB9912476.0		1999-05-28
GBGB9912476.0A GB9912476D0 (en)	1999-05-28	1999-05-28	Organic compounds

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Country Status (26)

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US (2)	US6432445B1 (de)
EP (1)	EP1181035B1 (de)
JP (1)	JP2003500454A (de)
KR (1)	KR20010111587A (de)
CN (1)	CN1353613A (de)
AT (1)	ATE291926T1 (de)
AU (1)	AU765935B2 (de)
BR (1)	BR0011030A (de)
CA (1)	CA2371247A1 (de)
CZ (1)	CZ20014214A3 (de)
DE (2)	DE10084671T1 (de)
ES (1)	ES2239605T3 (de)
GB (2)	GB9912476D0 (de)
HK (1)	HK1045642B (de)
HU (1)	HUP0201372A3 (de)
IL (1)	IL146186A0 (de)
MX (1)	MXPA01012222A (de)
NO (1)	NO20015785L (de)
NZ (1)	NZ515154A (de)
PL (1)	PL199591B1 (de)
PT (1)	PT1181035E (de)
RU (1)	RU2249461C2 (de)
SK (1)	SK285471B6 (de)
TR (1)	TR200103276T2 (de)
WO (1)	WO2000072867A2 (de)
ZA (1)	ZA200109658B (de)

Families Citing this family (27)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SK285019B6 (sk) *	1997-01-30	2006-04-06	Novartis Ag	Tvrdá želatínová tobolka
ATE404172T1 (de)	1998-12-30	2008-08-15	Dexcel Ltd	Dispergierbares konzentrat zur verabreichung von cyclosporin
GB9912476D0 (en) *	1999-05-28	1999-07-28	Novartis Ag	Organic compounds
AR033711A1 (es) *	2001-05-09	2004-01-07	Novartis Ag	Composiciones farmaceuticas
CA2471241A1 (en) *	2001-12-20	2003-07-03	Bernard Charles Sherman	Pharmaceutical compositions comprising a cyclosporin, a hydrophilic surfactant and a lipophilic surfactant
US20040115287A1 (en) *	2002-12-17	2004-06-17	Lipocine, Inc.	Hydrophobic active agent compositions and methods
US7538084B2 (en) *	2003-03-17	2009-05-26	Amr Technology, Inc.	Cyclosporins
JP2005255677A (ja) *	2004-02-12	2005-09-22	Nof Corp	シクロスポリン製剤
US20060014677A1 (en) *	2004-07-19	2006-01-19	Isotechnika International Inc.	Method for maximizing efficacy and predicting and minimizing toxicity of calcineurin inhibitor compounds
JP2008514701A (ja) *	2004-09-29	2008-05-08	エーエムアールテクノロジーインコーポレイテッド	シクロスポリンアルキン類似体およびそれらの薬学的使用
JP2008514702A (ja) *	2004-09-29	2008-05-08	エーエムアールテクノロジーインコーポレイテッド	新規シクロスポリン類似体およびそれらの薬学的使用
JP2008515886A (ja) *	2004-10-06	2008-05-15	エーエムアールテクノロジーインコーポレイテッド	シクロスポリンアルキンおよびそれらの医用薬剤としての有用性
AU2006235478B2 (en) *	2005-04-12	2011-07-21	Elan Pharma International Limited	Nanoparticulate and controlled release compositions comprising cyclosporine
WO2006114776A1 (en) *	2005-04-27	2006-11-02	Kingspan Holdings (Irl) Limited	Surfactant for phenolic foam
US7696165B2 (en) *	2006-03-28	2010-04-13	Albany Molecular Research, Inc.	Use of cyclosporin alkyne analogues for preventing or treating viral-induced disorders
US7696166B2 (en) *	2006-03-28	2010-04-13	Albany Molecular Research, Inc.	Use of cyclosporin alkyne/alkene analogues for preventing or treating viral-induced disorders
US11304960B2 (en)	2009-01-08	2022-04-19	Chandrashekar Giliyar	Steroidal compositions
MY158809A (en) *	2010-09-22	2016-11-15	Craun Res Sdn Bhd	Pharmaceutical compositions for calanolides, their derivatives and analogues, and process for producing the same
US20180153904A1 (en)	2010-11-30	2018-06-07	Lipocine Inc.	High-strength testosterone undecanoate compositions
US9034858B2 (en)	2010-11-30	2015-05-19	Lipocine Inc.	High-strength testosterone undecanoate compositions
US9358241B2 (en)	2010-11-30	2016-06-07	Lipocine Inc.	High-strength testosterone undecanoate compositions
US20120148675A1 (en)	2010-12-10	2012-06-14	Basawaraj Chickmath	Testosterone undecanoate compositions
WO2016033549A2 (en)	2014-08-28	2016-03-03	Lipocine Inc.	(17-ß)-3-OXOANDROST-4-EN-17-YL TRIDECANOATE COMPOSITIONS AND METHODS OF THEIR PREPARATION AND USE
US9498485B2 (en)	2014-08-28	2016-11-22	Lipocine Inc.	Bioavailable solid state (17-β)-hydroxy-4-androsten-3-one esters
US20160361322A1 (en)	2015-06-15	2016-12-15	Lipocine Inc.	Composition and method for oral delivery of androgen prodrugs
US11559530B2 (en)	2016-11-28	2023-01-24	Lipocine Inc.	Oral testosterone undecanoate therapy
WO2020018974A1 (en)	2018-07-20	2020-01-23	Lipocine Inc.	Liver disease

Citations (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1998033512A1 (en) *	1997-01-30	1998-08-06	Novartis Ag	Oil-free pharmaceutical compositions containing cyclosporin a
WO1998040094A1 (en) *	1997-03-12	1998-09-17	Abbott Laboratories	Hydrophilic binary systems for the administration of cyclosporine
WO2000040219A1 (en) *	1998-12-30	2000-07-13	Dexcel Ltd.	Dispersible concentrate for the delivery of cyclosporin

Family Cites Families (40)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL7012460A (de)	1970-08-22	1972-02-24
DE3225706C2 (de)	1982-07-09	1984-04-26	A. Nattermann & Cie GmbH, 5000 Köln	Flüssige Wirkstofformulierungen in Form von Konzentraten für Mikroemulsionen
DE3315805A1 (de)	1983-04-30	1984-11-08	Bayer Ag, 5090 Leverkusen	Wirkstoffzubereitungen
GB8903804D0 (en)	1989-02-20	1989-04-05	Sandoz Ltd	Improvements in or relating to organic compounds
US5639724A (en)	1984-07-24	1997-06-17	Sandoz Ltd.	Cyclosporin galenic forms
FR2609631A1 (fr)	1987-01-15	1988-07-22	Sanofi Sa	Compositions liquides stables a base de bithionol
US6007840A (en)	1988-09-16	1999-12-28	Novartis Ag	Pharmaceutical compositions comprising cyclosporins
US5342625A (en)	1988-09-16	1994-08-30	Sandoz Ltd.	Pharmaceutical compositions comprising cyclosporins
KR0148748B1 (ko)	1988-09-16	1998-08-17	장 크라메르, 한스 루돌프 하우스	사이클로스포린을 함유하는 약학조성물
DE3908047A1 (de)	1989-03-13	1990-09-20	Desitin Arzneimittel Gmbh	Hochdisperse pharmazeutische zusammensetzung
US5389688A (en)	1989-12-11	1995-02-14	Isp Investments Inc.	Water based microemulsion formulations
US5283229A (en)	1989-12-11	1994-02-01	Isp Investments Inc.	Delivery system for agricultural chemicals
US5266590A (en)	1989-12-11	1993-11-30	Isp Investments Inc.	Cold stabilization of aqueous microemulsions of a water-insoluble agriculturally active compound
US5110606A (en)	1990-11-13	1992-05-05	Affinity Biotech, Inc.	Non-aqueous microemulsions for drug delivery
EP0574492B1 (de)	1991-02-12	1999-05-12	Isp Investments Inc.	Stabilisierung von mikroemulsionen durch verwendung hydrophober saurer puffer
US5300529A (en)	1991-02-12	1994-04-05	Isp Investments Inc.	Stable, clear, efficacious aqueous microemulsion compositions containing a high loading of a water-insoluble, agriculturally active chemical
US6022853A (en) *	1991-08-30	2000-02-08	Creative Biomolecules, Inc.	Morphogen-enriched dietary composition
GB9225540D0 (en)	1992-12-07	1993-01-27	Ici Plc	Cleaning compositions
JPH06293633A (ja)	1993-04-05	1994-10-21	Shin Etsu Chem Co Ltd	水性腸溶性エマルジョンの製造方法
CH686761A5 (de)	1993-05-27	1996-06-28	Sandoz Ag	Galenische Formulierungen.
GB2278780B (en)	1993-05-27	1998-10-14	Sandoz Ltd	Macrolide formulations
FR2710535B1 (fr)	1993-09-30	1995-11-24	Gattefosse Ets Sa	Composition à usage pharmaceutique ou cosmétique apte à former une microémulsion.
DE4337041A1 (de)	1993-10-29	1995-05-04	Henkel Kgaa	Verfahren zur Herstellung in Öl-in-Wasser-Emulsionen
WO1995022343A1 (en)	1994-02-17	1995-08-24	Shiseido Company, Ltd.	Cyclosporin-containing emulsion composition
IL129547A (en)	1994-10-26	2001-01-11	Novartis Ag	Pharmaceutical compositions comprising a macrolide and an acid
US5691289A (en)	1994-11-17	1997-11-25	Kay Chemical Company	Cleaning compositions and methods of using the same
HU215966B (hu)	1994-11-21	1999-07-28	BIOGAL Gyógyszergyár Rt.	Orálisan alkalmazható, ciklosporint tartalmazó, összetett emulzió-előkoncentrátum
JPH11505257A (ja)	1995-05-19	1999-05-18	アボツト・ラボラトリーズ	親油性薬物の自己乳化性製剤
SE9503143D0 (sv)	1995-09-12	1995-09-12	Astra Ab	New preparation
DE19537836A1 (de)	1995-10-11	1997-04-17	Henkel Kgaa	Aerosolemulsionen
KR970064620A (ko)	1996-03-05	1997-10-13	임성기	사이클로스포린-함유 외용약제 조성물
DE19615271A1 (de)	1996-04-18	1997-10-23	Huels Chemische Werke Ag	Tensidhaltige Reinigungsmittel in Form einer Mikroemulsion
KR980008239A (ko)	1996-07-26	1998-04-30	김충환	사이클로스포린-함유 약학적 조성물
CA2283780A1 (en)	1997-03-12	1998-09-17	Abbott Laboratories	Lipophilic binary systems for the administration of lipophilic compounds
US6063762A (en)	1997-12-05	2000-05-16	Chong Kun Dang Corp.	Cyclosporin-containing microemulsion preconcentrate composition
US6028067A (en)	1997-12-05	2000-02-22	Chong Kun Dang Corp.	Cyclosporin-containing microemulsion preconcentrate composition
WO1999029335A1 (en)	1997-12-05	1999-06-17	Chong Kun Dang Corp.	Pharmaceutical composition containing cyclosporin
WO1999029316A1 (en)	1997-12-10	1999-06-17	Severson, Mary, L.	Pharmaceutical compositions containing an omega-3 fatty acid oil
NZ329929A (en) *	1998-03-09	1999-10-28	Bernard Charles Sherman	Pharmaceutical emulsion preconcentrate containing cyclosporin in a solvent system containing glycerides, propylene or polyethylene glycol, a surfactant and a co-surfactant
GB9912476D0 (en) *	1999-05-28	1999-07-28	Novartis Ag	Organic compounds

1999
- 1999-05-28 GB GBGB9912476.0A patent/GB9912476D0/en not_active Ceased
2000
- 2000-05-26 MX MXPA01012222A patent/MXPA01012222A/es active IP Right Grant
- 2000-05-26 JP JP2000620976A patent/JP2003500454A/ja active Pending
- 2000-05-26 KR KR1020017013293A patent/KR20010111587A/ko not_active Ceased
- 2000-05-26 DE DE10084671T patent/DE10084671T1/de not_active Withdrawn
- 2000-05-26 DE DE60019100T patent/DE60019100T2/de not_active Expired - Fee Related
- 2000-05-26 TR TR2001/03276T patent/TR200103276T2/xx unknown
- 2000-05-26 US US09/579,372 patent/US6432445B1/en not_active Expired - Fee Related
- 2000-05-26 BR BR0011030-2A patent/BR0011030A/pt not_active Application Discontinuation
- 2000-05-26 SK SK1722-2001A patent/SK285471B6/sk not_active IP Right Cessation
- 2000-05-26 PL PL351593A patent/PL199591B1/pl not_active IP Right Cessation
- 2000-05-26 PT PT00943742T patent/PT1181035E/pt unknown
- 2000-05-26 NZ NZ515154A patent/NZ515154A/en unknown
- 2000-05-26 CA CA002371247A patent/CA2371247A1/en not_active Abandoned
- 2000-05-26 WO PCT/EP2000/004829 patent/WO2000072867A2/en not_active Ceased
- 2000-05-26 GB GB0128277A patent/GB2367004B/en not_active Expired - Fee Related
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- 2000-05-26 RU RU2001133455/15A patent/RU2249461C2/ru not_active IP Right Cessation
- 2000-05-26 EP EP00943742A patent/EP1181035B1/de not_active Expired - Lifetime
- 2000-05-26 AU AU58100/00A patent/AU765935B2/en not_active Ceased
- 2000-05-26 CZ CZ20014214A patent/CZ20014214A3/cs unknown
- 2000-05-26 AT AT00943742T patent/ATE291926T1/de not_active IP Right Cessation
- 2000-05-26 ES ES00943742T patent/ES2239605T3/es not_active Expired - Lifetime
- 2000-05-26 CN CN00808183A patent/CN1353613A/zh active Pending
- 2000-05-26 IL IL14618600A patent/IL146186A0/xx unknown
2001
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2002
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Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1998033512A1 (en) *	1997-01-30	1998-08-06	Novartis Ag	Oil-free pharmaceutical compositions containing cyclosporin a
WO1998040094A1 (en) *	1997-03-12	1998-09-17	Abbott Laboratories	Hydrophilic binary systems for the administration of cyclosporine
WO2000040219A1 (en) *	1998-12-30	2000-07-13	Dexcel Ltd.	Dispersible concentrate for the delivery of cyclosporin

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
МАШКОВСКИЙ М.Д. Лекарственные средства. - М.: Медицина, 1993, ч.2, с.206-207. *

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US6767555B2 (en)	2004-07-27
JP2003500454A (ja)	2003-01-07
AU765935B2 (en)	2003-10-02
NO20015785L (no)	2002-01-23
ZA200109658B (en)	2002-08-20
CN1353613A (zh)	2002-06-12
HUP0201372A2 (en)	2002-09-28
EP1181035B1 (de)	2005-03-30
HK1045642B (en)	2005-10-28
KR20010111587A (ko)	2001-12-19
NO20015785D0 (no)	2001-11-27
GB0128277D0 (en)	2002-01-16
BR0011030A (pt)	2002-02-26
GB9912476D0 (en)	1999-07-28
DE60019100T2 (de)	2006-03-23
HUP0201372A3 (en)	2002-10-28
TR200103276T2 (tr)	2002-05-21
SK285471B6 (sk)	2007-02-01
AU5810000A (en)	2000-12-18
GB2367004A (en)	2002-03-27
WO2000072867A3 (en)	2001-04-05
EP1181035A2 (de)	2002-02-27
HK1045642A1 (en)	2002-12-06
ES2239605T3 (es)	2005-10-01
US20020188134A1 (en)	2002-12-12
NZ515154A (en)	2003-08-29
IL146186A0 (en)	2002-07-25
DE10084671T1 (de)	2002-06-06
US20020068083A1 (en)	2002-06-06
ATE291926T1 (de)	2005-04-15
PT1181035E (pt)	2005-08-31
MXPA01012222A (es)	2002-07-02
CA2371247A1 (en)	2000-12-07
PL199591B1 (pl)	2008-10-31
PL351593A1 (en)	2003-05-05
DE60019100D1 (de)	2005-05-04
WO2000072867A2 (en)	2000-12-07
SK17222001A3 (sk)	2002-03-05
CZ20014214A3 (cs)	2002-03-13
GB2367004B (en)	2004-04-14
US6432445B1 (en)	2002-08-13

Legal Events

Date	Code	Title	Description
2011-06-10	MM4A	The patent is invalid due to non-payment of fees	Effective date: 20100527

Publication	Publication Date	Title
RU2249461C2 (ru)	2005-04-10	Включающие циклоспорин композиции, практически не содержащие масла
US8575147B2 (en)	2013-11-05	Spontaneously dispersible N-benzoyl staurosporine compositions
JP2003500454A5 (de)	2007-07-19
EP1082119B1 (de)	2004-01-07	Piperidine substanz-p-antagonist enthaltende emulsionsvorkonzentrate
RU2235554C2 (ru)	2004-09-10	Предварительно приготовленные эмульсионные концентраты, содержащие циклоспорин или макролид
MXPA99006916A (en)	2000-01-01	Oil-free pharmaceutical compositions containing cyclosporin a
HK1035137B (en)	2004-09-30	Microemulsion preconcentrates containing a piperidine substance p antagonist